I'm not sure if this will help or hinder the debate - its my story....
I upgraded to iPad 3 or whatever it's called and had the same issues as the rest of you. Photos would not sync - 10 photos would go across and then without warning or error messages it would stop. I tried many things and read this forum. I sat down to try deleting caches and some of the other tricks in here that you have tried. I connected the iPad to iTunes thinking that I would tell it to stop syncing photos and so on.
You can guess what happened next - yes, it quietly sat there and synced all photos happily as though there had never been a problem. I have 2,500 photos ranging in size up to about 6.5MB that had no problem syncing to iPad 1 and iPhone. Now I have them on ipad3 too.
I see that they are not in the same order but I'm not going to worry about that. I hadn't "woken up" the iPad before the sync but it's hard to think that could be the silver bullet you're looking for. Thanks for all the helpful ideas in here and I hope that next time you connect up it works for you too.